WordNet

amino acid derived from tyrosine; has a sympathomimetic action; found in chocolate and cola drinks and ripe cheese and beer; "patients taking MAOIs should avoid foods containing tyramine"

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/02 09:17:40」(JST)

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Tyramine (4-hydroxyphenethylamine; para-tyramine, mydrial or uteramin) is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine.^[1] Tyramine acts as a catecholamine releasing agent. Notably, however, it is unable to cross the blood-brain barrier, resulting in only nonpsychoactive peripheral sympathomimetic effects. A hypertensive crisis can result from ingestion of tyramine-rich foods in conjunction with monoamine oxidase inhibitors (MAOIs).

Occurrence

Tyramine occurs widely in plants^[5] and animals, and is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include meats that are potentially spoiled or pickled, aged, smoked, fermented, or marinated (some fish, poultry, and beef); most pork (except cured ham); chocolate; alcoholic beverages; and fermented foods, such as most cheeses (except ricotta, cottage, cream and Neufchâtel cheeses), sour cream, yogurt, shrimp paste, soy sauce, soybean condiments, teriyaki sauce, tempeh, miso soup, sauerkraut, kimchi, broad (fava) beans, green bean pods, Italian flat (Romano) beans, snow peas, edamame, avocados, bananas, pineapple, eggplants, figs, red plums, raspberries, peanuts, Brazil nuts, coconuts, processed meat, yeast, and an array of cacti.

Physical effects and pharmacology

Evidence for the presence of tyramine in the human brain has been confirmed by postmortem analysis.^[6] Additionally, the possibility that tyramine acts directly as a neurotransmitter was revealed by the discovery of a G protein-coupled receptor with high affinity for tyramine, called TAAR1.^[7]^[8] The TAAR1 receptor is found in the brain, as well as peripheral tissues, including the kidneys.^[9]

Tyramine is physiologically metabolized by MAO_A. In humans, if monoamine metabolism is compromised by the use of monoamine oxidase inhibitors (MAOIs) and foods high in tyramine are ingested, a hypertensive crisis can result, as tyramine can also displace stored monoamines, such as dopamine, norepinephrine and epinephrine, from pre-synaptic vesicles. The first signs of this were discovered by a neurologist who noticed his wife, who at the time was on MAOI medication, had severe headaches when eating cheese.^[10] For this reason, the crisis is still called the "cheese effect" or "cheese crisis", though other foods can cause the same problem.^[11]^:30–31 Most processed cheeses do not contain enough tyramine to cause hypertensive effects, although some aged cheeses (such as Stilton) do.^[12]^[13]

A large dietary intake of tyramine (or a dietary intake of tyramine while taking MAO inhibitors) can cause the tyramine pressor response, which is defined as an increase in systolic blood pressure of 30 mmHg or more. The displacement of norepinephrine (noradrenaline) from neuronal storage vesicles by acute tyramine ingestion is thought to cause the vasoconstriction and increased heart rate and blood pressure of the pressor response. In severe cases, adrenergic crisis can occur.^{[medical citation needed]}

However, if one has had repeated exposure to tyramine, there is a decreased pressor response; tyramine is degraded to octopamine, which is subsequently packaged in synaptic vesicles with norepinephrine (noradrenaline)^{[citation needed]}. Therefore, after repeated tyramine exposure, these vesicles contain an increased amount of octopamine and a relatively reduced amount of norepinephrine. When these vesicles are secreted upon tyramine ingestion, there is a decreased pressor response, as less norepinephrine is secreted into the synapse, and octopamine does not activate alpha or beta adrenergic receptors.^{[medical citation needed]}

When using a MAO inhibitor (MAOI), the intake of approximately 10 to 25 mg of tyramine is required for a severe reaction compared to 6 to 10 mg for a mild reaction.^{[medical citation needed]}

Research reveals a possible link between migraine and elevated levels of tyramine. A 2007 review published in Neurological Sciences^[14] presented data showing migraine and cluster headaches are characterised by an increase of circulating neurotransmitters and neuromodulators (including tyramine, octopamine and synephrine) in the hypothalamus, amygdala and dopaminergic system.

Biosynthesis

Biochemically, tyramine is produced by the decarboxylation of tyrosine via the action of the enzyme tyrosine decarboxylase.^[15] Tyramine can, in turn, be converted to methylated alkaloid derivatives N-methyltyramine, N,N-dimethyltyramine (hordenine), and N,N,N-trimethyltyramine (candicine).

Tyramine
N-Methyltyramine
N,N-Dimethyltyramine (hordenine)
N,N,N-Trimethyltyramine (candicine)

In humans, tyramine is produced from tyrosine, as shown in the following diagram.

Human biosynthesis pathway for trace amines and catecholamines^[16]

L-Phenylalanine

L-Tyrosine

L-Dopa

Epinephrine

Phenethylamine

p-Tyramine

Dopamine

Norepinephrine

N-Methylphenethylamine

N-Methyltyramine

p-Octopamine

Synephrine

3-Methoxytyramine

AADC

PNMT

AAAH

COMT

DBH

In humans, catecholamines and phenethylaminergic trace amines are derived from the amino acid phenylalanine.

Chemistry

In the laboratory, tyramine can be synthesized in various ways, in particular by the decarboxylation of tyrosine.^[17]^[18]^[19]

Legal status

United States

Tyramine is not scheduled at the federal level in the United States and is therefore legal to buy, sell, or possess.^[20]

Florida

Tyramine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in pure form.^[21]

References

^ ^a ^b PubChem
^ Andersen A. M. (1977). "The crystal and molecular structure of tyramine hydrochloride". Acta Chem. Scandinavica B 31: 162–166.
^ ^a ^b ^c The Merck Index, 10th Ed. (1983), p.1405, Rahway: Merck & Co.
^ Kappe, T. (1965). Journal of Medicinal Chemistry 8: 368–374. doi:10.1021/jm00327a018 Missing or empty |title= (help)
^ T. A. Smith (1977) Phytochem. 16 9-18.
^ Philips, Rozdilsky, Boulton (Feb 1978). "Evidence for the presence of m-tyramine, p-tyramine, tryptamine, and phenylethylamine in the rat brain and several areas of the human brain.". Biological Psychiatry, 13 (1): 51–57. PMID 623853.
^ Navarro, Gilmour, Lewin (10 July 2006). "A Rapid Functional Assay for the Human Trace Amine-Associated Receptor 1 Based on the Mobilization of Internal Calcium". J Biomol Screen 11 (6): 668–693. doi:10.1177/1087057106289891. PMID 16831861.
^ Liberles, Buck (10 August 2006). "A second class of chemosensory receptors in the olfactory epithelium". Nature 441 (7103): 645–650. doi:10.1038/nature05066. PMID 16878137.
^ Xie, Westmoreland, Miller (May 2008). "Modulation of monoamine transporters by common biogenic amines via trace amine-associated receptor 1 and monoamine autoreceptors in human embryonic kidney 293 cells and brain synaptosomes.". J. Pharm. 441 (2): 629–640. doi:10.1124/jpet.107.135079. PMID 18310473.
^ Sathyanarayana Rao TS and Vikram K. Yeragani VK (2009) Hypertensive crisis and cheese Indian J Psychiatry. 51(1): 65–66.
^ E. Siobhan Mitchell Antidepressants, chapter in Drugs, the Straight Facts, edited by David J. Triggle. 2004, Chelsea House Publishers
^ Stahl SM, Felker A (2008). "Monoamine oxidase inhibitors: a modern guide to an unrequited class of antidepressants". Cns Spectrums 13 (10): 855–870. PMID 18955941.
^ Tyramine-restricted Diet 1998, W.B. Saunders Company.
^ D'Andrea, G; Nordera, GP; Perini, F; Allais, G; Granella, F (May 2007). "Biochemistry of neuromodulation in primary headaches: focus on anomalies of tyrosine metabolism". Neurological Sciences. 28, Supplement 2 (S2): S94–S96. doi:10.1007/s10072-007-0758-4. PMID 17508188
^ Tyrosine metabolism - Reference pathway, Kyoto Encyclopedia of Genes and Genomes (KEGG)
^ ^[1]^[2]
^ G. Barger (1909). J. Chem. Soc. 95: 1123. Missing or empty |title= (help)
^ Waser, Ernst (1925). "Untersuchungen in der Phenylalanin-Reihe VI. Decarboxylierung des Tyrosins und des Leucins". Helvetica Chimica Acta 8: 758. doi:10.1002/hlca.192500801106.
^ Buck, Johannes S. (1933). Journal of the American Chemical Society 55 (8): 3388. doi:10.1021/ja01335a058. Missing or empty |title= (help)
^ §1308.11 Schedule I.
^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

^ Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines". Pharmacol. Ther. 125 (3): 363–375. doi:10.1016/j.pharmthera.2009.11.005. PMID 19948186.
^ Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends Pharmacol. Sci. 26 (5): 274–281. doi:10.1016/j.tips.2005.03.007. PMID 15860375.

UpToDate Contents

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1. 成人におけるうつ病治療としてのモノアミン酸化酵素阻害剤（MAOI） monoamine oxidase inhibitors maois for treating depressed adults
2. 褐色細胞腫の臨床症状および診断 clinical presentation and diagnosis of pheochromocytoma
3. 成人における高血圧緊急症の評価および治療 evaluation and treatment of hypertensive emergencies in adults
4. 傍神経節腫：疫学、臨床症状、診断、および組織学的検査 paragangliomas epidemiology clinical presentation diagnosis and histology
5. 成人における社会不安障害に対する薬物療法 pharmacotherapy for social anxiety disorder in adults

English Journal

Fast determination of biogenic amines in beverages by a core-shell particle column.

Preti R1, Antonelli ML2, Bernacchia R3, Vinci G3.
Food chemistry.Food Chem.2015 Nov 15;187:555-62. doi: 10.1016/j.foodchem.2015.04.075. Epub 2015 Apr 24.
A fast and reliable HPLC method for the determination of 11 biogenic amines in beverages has been performed. After pre-column derivatization with dansyl-chloride a Kinetex C18 core-shell particle column (100mm×4.6mm, 2.6μm particle size) has been employed and the biogenic amines were identified an
PMID 25977063

Resolution of quaternary mixtures of cadaverine, histamine, putrescine and tyramine by the square wave voltammetry and partial least squares method.

Henao-Escobar W1, Domínguez-Renedo O2, Alonso-Lomillo MA3, Arcos-Martínez MJ4.
Talanta.Talanta.2015 Oct 1;143:97-100. doi: 10.1016/j.talanta.2015.05.047. Epub 2015 May 23.
This work presents the simultaneous determination of cadaverine, histamine, putrescine and tyramine by square wave voltammetry using a boron-doped diamond electrode. A multivariate calibration method based on partial least square regressions has allowed the resolution of the very high overlapped vol
PMID 26078134

Tetragenococcus koreensis is part of the microbiota in a traditional Italian raw fermented sausage.

Amadoro C1, Rossi F2, Piccirilli M3, Colavita G3.
Food microbiology.Food Microbiol.2015 Sep;50:78-82. doi: 10.1016/j.fm.2015.03.011. Epub 2015 Apr 8.
This study reports the isolation of Tetragenococcus koreensis, a bacterial species currently represented only by the type strain isolated from kimchi, from a raw fermented and ripened Italian sausage, Ventricina Vastese, all over the ripening period of five months. Rep-PCR genotyping showed that dif
PMID 25998818

Japanese Journal

2P-109 草本系モデル植物ブラキポディウム由来芳香族脱炭酸酵素を用いた酵母によるチラミン合成(代謝工学,一般講演)

日本生物工学会大会講演要旨集 66, 134, 2014-08-05
NAID 110009906493

Analysis of plasmids encoding the tyrosine decarboxylase gene in Tetragenococcus halophilus isolated from fish sauce

Fisheries science 80(4), 849-858, 2014-07
NAID 40020126005

Quantitative Structure-Cytotoxicity Relationship of Phenylpropanoid Amides

Anticancer Research 34(7), 3543-3548, 2014-07
NAID 120005520989

Related Pictures

★リンクテーブル★

リンク元	「チラミン」
拡張検索	「colestyramine」

「チラミン」

Tyramine
Names
	IUPAC name 4-(2-aminoethyl)phenol
Identifiers
CAS Registry Number	51-67-2
ChEBI	CHEBI:15760
ChEMBL	ChEMBL11608
ChemSpider	5408
	InChI InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2 ; Key: DZGWFCGJZKJUFP-UHFFFAOYSA-N ; InChI=1/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2; Key: DZGWFCGJZKJUFP-UHFFFAOYAB ;
Jmol-3D images	Image
KEGG	C00483
MeSH	Tyramine
PubChem	5610
	SMILES Oc1ccc(cc1)CCN ;
UNII	X8ZC7V0OX3
Properties
Chemical formula	C8H11NO
Molar mass	137.179 g/mol
Appearance	colorless solid
Density	1.20 g/cm 3
Melting point	164 to 165 °C (327 to 329 °F; 437 to 438 K)
Boiling point	205 to 207 °C (401 to 405 °F; 478 to 480 K) at 25 mmHg; 166 °C at 2 mmHg
Solubility in water	1 g in 95 mL at 15 °C
Acidity (pKa)	9.74 (OH); 10.52 (NH3+)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	Infobox references

　　[★]

英: tyramine
同: p-ヒドロキシフェニルエチルアミン p-hydroxyphenylethylamine
関: MAO inhibitor

特徴

ノルアドレナリンの放出を促進する→レセルピンで処理されると作用が消失
チーズ、赤ワイン、ビール、にしん、鶏肝、チョコレートに多く含まれる

薬理作用

間接的にアドレナリン受容体を刺激する。

シナプス前膜からノルアドレナリンの分泌を促すことによる

適応

気管支喘息

→β受容体作動薬に取って代わられる

鼻づまり

→α受容体作動薬に取って代わられる

※　鼻粘膜にはα受容体しかない

脊髄・硬膜外麻酔の低血圧に対する対処
ナルコプシー
夜尿症

注意

タキヒラキシス tachyphylaxisを起こしやすい
コカイン、三環系抗うつ薬(imipramine, desipramine)がuptake1を抑制
MAO阻害薬を使用している場合、チラミンが投与されると神経終末中のノルアドレナリンの分解が押さえられてシナプス小胞内の貯蔵量がまし、チラミンにより大量のノルアドレナリンが放出される→高血圧発作(クリーゼ)を起こす。

「colestyramine」

　　[★]

コレスチラミン

関: cholestyramine

[pubchem-1] PubChem

[2] Andersen A. M. (1977). "The crystal and molecular structure of tyramine hydrochloride". Acta Chem. Scandinavica B 31: 162–166.

[Merck-3] The Merck Index, 10th Ed. (1983), p.1405, Rahway: Merck & Co.

[4] Kappe, T. (1965). Journal of Medicinal Chemistry 8: 368–374. doi:10.1021/jm00327a018 Missing or empty |title= (help)

[5] T. A. Smith (1977) Phytochem. 16 9-18.

[6] Philips, Rozdilsky, Boulton (Feb 1978). "Evidence for the presence of m-tyramine, p-tyramine, tryptamine, and phenylethylamine in the rat brain and several areas of the human brain.". Biological Psychiatry, 13 (1): 51–57. PMID 623853.

[7] Navarro, Gilmour, Lewin (10 July 2006). "A Rapid Functional Assay for the Human Trace Amine-Associated Receptor 1 Based on the Mobilization of Internal Calcium". J Biomol Screen 11 (6): 668–693. doi:10.1177/1087057106289891. PMID 16831861.

[8] Liberles, Buck (10 August 2006). "A second class of chemosensory receptors in the olfactory epithelium". Nature 441 (7103): 645–650. doi:10.1038/nature05066. PMID 16878137.

[9] Xie, Westmoreland, Miller (May 2008). "Modulation of monoamine transporters by common biogenic amines via trace amine-associated receptor 1 and monoamine autoreceptors in human embryonic kidney 293 cells and brain synaptosomes.". J. Pharm. 441 (2): 629–640. doi:10.1124/jpet.107.135079. PMID 18310473.

[10] Sathyanarayana Rao TS and Vikram K. Yeragani VK (2009) Hypertensive crisis and cheese Indian J Psychiatry. 51(1): 65–66.

[11] E. Siobhan Mitchell Antidepressants, chapter in Drugs, the Straight Facts, edited by David J. Triggle. 2004, Chelsea House Publishers

[12] Stahl SM, Felker A (2008). "Monoamine oxidase inhibitors: a modern guide to an unrequited class of antidepressants". Cns Spectrums 13 (10): 855–870. PMID 18955941.

[13] Tyramine-restricted Diet 1998, W.B. Saunders Company.

[14] D'Andrea, G; Nordera, GP; Perini, F; Allais, G; Granella, F (May 2007). "Biochemistry of neuromodulation in primary headaches: focus on anomalies of tyrosine metabolism". Neurological Sciences. 28, Supplement 2 (S2): S94–S96. doi:10.1007/s10072-007-0758-4. PMID 17508188

[15] Tyrosine metabolism - Reference pathway, Kyoto Encyclopedia of Genes and Genomes (KEGG)

[Trace_amine_template_grouped_ref-16] [1]^[2]

[17] G. Barger (1909). J. Chem. Soc. 95: 1123. Missing or empty |title= (help)

[18] Waser, Ernst (1925). "Untersuchungen in der Phenylalanin-Reihe VI. Decarboxylierung des Tyrosins und des Leucins". Helvetica Chimica Acta 8: 758. doi:10.1002/hlca.192500801106.

[19] Buck, Johannes S. (1933). Journal of the American Chemical Society 55 (8): 3388. doi:10.1021/ja01335a058. Missing or empty |title= (help)

[PART_1308_.E2.80.94_SCHEDULES_OF_CONTROLLED_SUBSTANCES_-_1308.11_Schedule_I-20] §1308.11 Schedule I.

[Florida_Statutes_-_Chapter_893_-_DRUG_ABUSE_PREVENTION_AND_CONTROL-21] Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

[Trace_amine_template_1-22] Broadley KJ (March 2010). "The vascular effects of trace amines and amphetamines". Pharmacol. Ther. 125 (3): 363–375. doi:10.1016/j.pharmthera.2009.11.005. PMID 19948186.

[Trace_amine_template_2-23] Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends Pharmacol. Sci. 26 (5): 274–281. doi:10.1016/j.tips.2005.03.007. PMID 15860375.

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案内

tyramine